US4007191A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-(Piperidinyl or tetrahydropyridinyl)-alkyl)-2,3-dihydro-3-hydroxy-1H-benz(DE)isoquinolin-1-ones
Assignee: ER Squibb and Sons LLC
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Filing: 1975-10-14
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Granted: 1977-02-08
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Expires: 1995-10-14
Abstract
Abstract Compounds of the following formula ##STR1## wherein R 1 and R 2 are selected from hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen, trifluoromethyl, nitro, amino and cyano; Z is selected from ##STR2## R 3 is selected from phenyl, phenyl-lower alkyl, substituted phenyl, and substituted phenyl-lower alkyl; R 4 is selected from R 3 and a 6-membered unsaturated substituted or unsubstituted heterocyclic ring selected from pyridine, diazine and triazine; and A is a straight or branched chain alkylene of 2 to 8 carbons are disclosed. These compounds exhibit antidepressant activity.
Inventors
- 👤 Peter C. Wade
- 👤 Berthold Richard Vogt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:18
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/14; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
125 words
A compound of the formula: ##STR64## wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl, nitro, amino and cyano; Z is selected from the group consisting of ##STR65## wherein the dashed line indicates the optional presence of a double bond; R 3 is selected from the group consisting of phenyl, phenyl-lower alkyl, substituted phenyl and substituted phenyl-lower alkyl wherein said substituent is one or two members selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, halogen, amino, nitro, and trifluoromethyl provided that only one phenyl substituent is selected from amino, nitro, trifluoromethyl, and lower alkylthio; and A is straight or branched chain alkylene of 2 to 8 carbons.
Claim 2
Dependent Claim
125 words
A compound of the formula: ##STR64## wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, trifluoromethyl, nitro, amino and cyano; Z is selected from the group consisting of ##STR65## wherein the dashed line indicates the optional presence of a double bond; R 3 is selected from the group consisting of phenyl, phenyl-lower alkyl, substituted phenyl and substituted phenyl-lower alkyl wherein said substituent is one or two members selected from the group consisting of lower alkyl, lower alkoxy, lower alkylthio, halogen, amino, nitro, and trifluoromethyl provided that only one phenyl substituent is selected from amino, nitro, trifluoromethyl, and lower alkylthio; and A is straight or branched chain alkylene of 2 to 8 carbons.
Claim 3
Dependent Claim
153 words
The compound of claim 1 of the formula: ##STR66## wherein R 1 and R 2 are the same and are located at the 7- and 6-positions or the 8- and 5-positions respectively and are selected from the group consisting of hydrogen, lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, trifluoromethyl, halogen, amino, nitro and cyano; and R 3 is selected from the group consisting of phenyl, phenyl-lower alkyl, substituted phenyl, and substituted phenyl-lower alkyl wherein said lower alkyl is of 1 to 4 carbons and said phenyl substituent is one or two members selected from the group consisting of lower alkyl of 1 to 4 carbons, lower alkoxy of 1 to 4 carbons, lower alkylthio of 1 to 4 carbons, halogen, amino, nitro and trifluoromethyl provided that only one phenyl substituent is selected from amino, nitro, trifluoromethyl, and lower alkylthio.
Claim 4
Dependent Claim
82 words
The compound of claim 2 wherein R 1 and R 2 are selected from the group consisting of hydrogen, Cl, Br, F, methyl and methoxy; Z is ##STR67## wherein the dashed line indicates the optional presence of a double bond; R 3 is selected from the group consisting of phenyl, benzyl, phenethyl, monosubstituted phenyl, monosubstituted benzyl, and monosubstituted phenethyl wherein said substituent is Cl, Br, F, methyl or methoxy; and A is straight or branched chain alkylene of 2 to 6 carbons.
Claim 5
Dependent Claim
28 words
The compound of claim 3 wherein R 1 and R 2 are both hydrogen; Z is ##STR68## and A is straight chain alkylene of 2 to 6 carbons.
Claim 6
Dependent Claim
13 words
The compound of claim 4 wherein A is --(CH 2 ) 2 --.
Claim 7
Dependent Claim
13 words
The compound of claim 4 wherein A is --(CH 2 ) 3 --.
Claim 8
Dependent Claim
13 words
The compound of claim 4 wherein A is --(CH 2 ) 4 --.
Claim 9
Dependent Claim
13 words
The compound of claim 4 wherein A is --(CH 2 ) 5 --.
Claim 10
Dependent Claim
13 words
The compound of claim 4 wherein A is --(CH 2 ) 6 --.
Claim 11
Dependent Claim
28 words
The compound of claim 3 wherein R 1 and R 2 are both hydrogen; Z is ##STR69## and A is straight chain alkylene of 2 to 6 carbons.
Claim 12
Dependent Claim
13 words
The compound of claim 10 wherein A is --(CH 2 ) 2 --.
Claim 13
Dependent Claim
13 words
The compound of claim 10 wherein A is --(CH 2 ) 3 --.
Claim 14
Dependent Claim
13 words
The compound of claim 10 wherein A is --(CH 2 ) 4 --.
Claim 15
Dependent Claim
13 words
The compound of claim 10 wherein A is --(CH 2 ) 5 --.
Claim 16
Dependent Claim
13 words
The compound of claim 10 wherein A is --(CH 2 ) 6 --.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-08 | 1980-08-09 | 1981-02-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-08 | 1984-08-09 | 1985-02-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-08 | 1988-08-09 | 1989-02-08 | $7700.00 | Window Closed / Lapsed |